Pigment dyestuffs



l 'atentecl Sept. 20, 1932 UNITED srarss Parent orricn WINFRID HENTRICH AND MAX HABDTMANN, OF WIESDORF-ON-THE-RI-HNE, GER- MANY, ASSIGNORS TO GENERAL ANILINE WORKS, INC., OF NEW YORK, N. Y., A

CORPORATION OF DELAWARE PIGMENT DYES'IUFFS N0 Drawing. Application filed September 19, 1929, Serial No. 393,838, and in Germany September 22, 1928.

The present invention relates to new water resistant pigment dyestuffs, more partlcularly it relates to pigment dyestuffs of the general formula wherein R stands for an aromatic nucleus of the benzene or naphthalene series which is at least once substituted by a halogen atom and which may be further substituted by alkyl, alkoxy or a carboXylic acid group, and Me stands for an alkaline earth metal atom, the group SO Me standing in 6 or 7 position.

Our new pigment dyestuffs are obtainable by diazotizing in the usual manner a suitable aromatic amine being at least once substituted by a halogen atom, coupling the diazo compound with 2-naphthol-6-(or 7 -sulfonic acid and precipitating the pigment dyestufi by adding to the solution of the azo dyestuff an aqueous solution of a salt of an alkali earth metal, such as barium or calcium chlo ride, and if desired in the presence of a suitable substratum, for example heavy spar and magnesia usta.

Our new pigment dyestuffs, in particular the calcium and barium pigment dyestufis or lacquers, possess excellent resistivity to Water and oil besides satisfactory fastness to light. The shade of the new substances gerlierally varies between yellow and bluish rec The invention is illustrated by the following example, but is not restricted thereto A dyestufl? composition capable of being used in the low pressure process is prepared as follows :-17 parts of gilso-nite-asphalt are dissolved at 40 50 C. in 40 parts of Xylene.

To this solution there are added while thoroughly stirring 2-8 parts of the barium salt of the dyestuff 2-chloro-aniline-azo-2-naphthol-G-sulfonic acid and 14-15 parts of magnesia usta, made into a paste with 26 parts of Xylene. mass is brightened in addition, with a small quantity of a fast soluble dyestufii'.

Printings produced with this low pressure paste are completely water-resistant after drying.

The following table of useful pigment dyestuifs or lacquers serves to further illustrate the invention by Way of example 2-- 'Diazo component Coupling component Shade Z-chloroaniline 3-chloroaniiine 2 naphthol 6 sulfonic 2 naphthol 6 sulfonic acid.

2 naphthol 6 sulfonic Reddish-orange Orange 7 6-chloro-2-toluidine 4.6-dich1oro-2-toluidine 4 chloro 2.5 dimethyl-l-aminobenzene 2-chloro-4-toluidine 4-chl0ro-2-anisidine 1-chi0ro-2-napl1thylam ine 4-ch1oroanthr anilic acid 2-chloroaniline 2 naphthol 6 sulfonic 2 naphthol- 6 -sulfonic 2- naphthol 6 sulfonic 2 naphthol 6 sulfonic acid 2 naphthol 6 sulfonic acid 2 naphthol 6 sulfonic acid 2 naphthol 6 sulionic 2 naphthol 7 sulfonic acid Ba: Red-orange Orange Orange Yellowish-red Orange Bordeaur Brown red Ca: Yellow-red Ba: Blue-red Orange (reddish) We claim 1. As new products thep of the probable general formulav e? l2 igment dyestuffs When desired or necessary the wherein R stands for an aromatic nucleus of, the benezene or naphthalene series which is at least once substituted by a halogen atom and whch may be further substituted by a .substituent'of the group consisting of alkyl,

alkoxy and the carbo-xylic acid group and wherein Me stands for an alkaline earth metal atom, the group some standing in one of the positions 6 and 7, said compounds being generally yellow to bluish red powders, possessing an excellent resistivity to water and oil and a satisfactory fastness to light, and being valuable dyestuffs in printing processes.

2. As new products the pigment dyestuffs of the probable general formula wherein Hal stands for a halogen atom, Me

stands for an alkaline earth metal atom,

the group SO Me standing .in one of the po-sitions6 and 7 and wherein'the benzene nucleus may be further substituted by a substituent of the group consisting of alkyl,

alkoxy and the carboxylic acid group, said compounds being generally yellow to bluish red powders, possessing an excellent resistivity to water and oil'and a satisfactory fastness to light, and being valuable dyestuffs in printing processes.

. 3. As new products the. pigment dyestuffs Q of the probable general formula wherein Cl stands in one of the positions 2 and 4 and wherein the benzene nucleus B may be further substituted by a substituent of the group consisting ofalkyl, alkoxy and the carboxylic acid group, Me stands fora .metal atom of the group consisting of barium and calcium, the group SO Me standing in one of the positions 6 and 7, said compounds being generally yellow to bluish red powders, possessingan excellent resistivity to water and oil and a satisfactory fastness to light, and being valuable dyestuffs in printing processes. f

4. As a new pro-duct the barium salt of V the dyestuff 2-chloro-aniline-azo-2-naphthol- 6-su1fonic acid, being a reddish-orange powder, possessing an excellent resistivity to water and oil and a satisfactory fastness to light, and being a valuable dyestufi in printlng processes. V In testimony whereof, we afiix our signatures. i r r WINFRID HENTRICH. [L. s MAX HAQRDTMANN. [L. s.] 

